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The Chianti region is full of beautiful historical villas. These lodgings are exclusive accommodations of great charm; perfect if you wish to experience the luxury and elegance typical of Florentine noble families, that used to have their own villa in the countryside. Chianti villas have been carefully restored to their former splendour and offer refined and charming accommodations fully equipped with all modern comforts and facilities.

33 Properties Found


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Villa Piaggia

Luxury Villa For Rent in Tuscany Near San Gimignano

  • rooms: 9
  • sleeps: 17
  • Location: Montaione (Countryside)

Villa Piaggia, located in Montaione near San Gimignano, is an exclusive and elegant villa that can host up to 17 guests. The villa and its swimming pool is surrounded by a large park and vineyards, enjoying a beautiful view over the Tuscan countryside.

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Villa Dianella

Villa BB De Charme in Vinci Near Florence

  • rooms: 4
  • sleeps: 8
  • Location: Vinci (Countryside)

Small elegant bed and breakfast near Vinci in a beautiful Medicean villa. The gardens are the perfect setting for weddings and special meetings, with views over the surrounding vineyards and olive groves.

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Il Cellese

Apartments in Chianti Farmhouse with Pool Near Siena

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  • apartments: 7
  • sleeps: 25
  • Location: Castellina in Chianti (Countryside)
  • weekly price: from € 400 to € 2100

Located in Castellina in Chianti, in the heart of Chianti area, this typical Tuscan farmhouse offers 7 independent apartments and a gorgeous villa, a large salt water pool with view on the surrounding hills and restaurant.

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Villa il Poggiale

Country Resort & Relais in Chianti near Florence

  • apartments: 1
  • rooms: 24
  • sleeps: 48
  • Location: San Casciano in Val di Pesa (Countryside)
  • daily price: from € 80 to € 400

This villa B&B is situated in a stunning location, surrounded by the marvellous nature of Chianti. It offers cozy, spacious and romantic rooms provided with all modern comforts, a Tuscan restaurant with organic products, a spa and swimming pool.

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Villa Le Torri

Holiday Apartments in Chianti Villa

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  • apartments: 9
  • sleeps: 26
  • Location: Montespertoli (Countryside)
  • weekly price: from € 485 to € 1005

Stone villa from the 13th century offers apartments for your vacation in the Chianti hills near Florence. Managed directly by the owners, guests receive personal attention and service while enjoying the self-catering accommodation and the villa's pool.

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Villa Vianci

A luxurious Villa in Chianti near Siena

  • rooms: 6
  • sleeps: 12
  • Location: Poggibonsi (Countryside)

Villa Vianci is a family run luxury rental between the hills of Chianti and the historic city of Siena. There is a beautiful green garden with pool, lots of family space throughout the villa for up to 12 PAX on holiday in Tuscany

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Villa di Cabbiavoli

Exclusive Chianti Villa With Pool

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  • sleeps: 12
  • Location: Castelfiorentino (Countryside)

An ancient castle sitting on the gentle hills of Chianti, finely restored and turned into a beautiful luxury villa perfect for 12 people. It offers a private, gorgeous outdoor pool and exclusive services to make your stay unforgettable.

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Torre a Cona

Luxurious villa with pool for an exclusive stay in Chianti area

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  • apartments: 9
  • rooms: 4
  • sleeps: 42
  • Location: Rignano sull'Arno (Countryside)
  • daily price: from € 120 to € 530
  • weekly price: from € 600 to € 4700

Charming farmhouse with pool situated in the Chianti area near Florence. It offers rooms and independent apartments, all recently restored and finely decorated and a huge, wide park surrounded by hectars of olive trees and vineyards.

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Tenuta Moriano

Chianti Farmhouse with Delightful Apartments

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  • apartments: 20
  • rooms: 20
  • sleeps: 58
  • Location: Montespertoli (Countryside)
  • daily price: from € 80 0
  • weekly price: from € 480 to € 1435

Immersed in the green hills of Chianti, in a typical Tuscan landscape, this beautiful farmhouse offers spacious apartments equipped with all amenities. Guests can enjoy a beautiful pool, tennis court and guided tasting of the farm's excellent wines.

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Borgo Argenina

B&B and Private Villas in Gaiole in Chianti

  • sleeps: 22
  • Location: Gaiole in Chianti (Countryside)
  • daily price: from € 160 to € 420

A romantic & enchanting way to discover the mysteries of Tuscany at Borgo Argenina, where the B&B and private villas combine the savour perfumes from the kitchen, and the warm hospitality of your hostess for a memorable holiday adventure.

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Podere Villa Bassa

Holiday Home Rental Overlooking the Stupendous Chianti Countrysid

  • apartments: 2
  • sleeps: 18
  • Location: Montespertoli (Countryside)
  • weekly price: from € 1190 to € 2270

The two extra large vacation rental apartments at Podere Villabassa near Montespertoli, feature fantastic gardens, terraces, pool & hot tub. The holiday accommodations can be combined into one large villa with communicating doors for groups of 18 PAX

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Il Corbezzolo

Private Romantic Holiday Villa Rental near San Gimignano

  • sleeps: 4
  • Location: Gambassi Terme (Countryside)
  • weekly price: from € 750 to € 980

A one bedroom private villa rental for vacation near San Gimignano and Chianti, promises tranquility, comfort & romantic Tuscan landscapes for your holiday. Perfect base also for a honeymoon.

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Villa Fillinelle

Luxury Accommodations near Florence: B&B or Vacation Villa

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  • apartments: 1
  • rooms: 3
  • sleeps: 12
  • Location: Tavarnelle Val di Pesa (Countryside)
  • daily price: from € 180 to € 280
  • weekly price: from € 0 6000

Lush gardens, charming decors & panoramic views. This prestigious medieval Villa has been totally restored for your holiday near Chianti & Florence. It offers two perfect solutions: 4 charming B&B rooms or the entire villa for a deluxe holiday.

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Borgo della Meliana

Charming Resort Apartments in Villa in Gambassi Terme

  • apartments: 11
  • sleeps: 32
  • Location: Gambassi Terme (Countryside)

Located in Gambassi Terme, near San Gimignano, in the heart of Tuscany, Borgo della Meliana offers elegant apartments decorated with antiques. This charming resort offers two external pools and common areas with bbq.

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Agriturismo Colognole

Villa Farmhouse in Rufina near Florence

  • apartments: 6
  • rooms: 4
  • sleeps: 53
  • Location: Pontassieve (Countryside)
  • daily price: from € 48 to € 680
  • weekly price: from € 290 to € 3400

Marvellous setting for this rural countryhouse in the heart of Chianti, with easy access to Florence. Clean, tiny and lovely accommodation in rooms, apartments or independent villas.

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Your Summer Residence

Many villas in Chianti are historical homes, dating back to the Renaissance, when wealthy Florentine and Sienese families used to move to their summer residences to escape the heat of the city.

After a careful restoration, they have been beautifully converted in many different types of accommodations: hotels, bed and breakfast, and fully equipped apartments.

They also offer a number of amenities and services, such as swimming pool, spa, good restaurants, guided tours and excursions, horse back riding, wine tastings, and much more. Chianti villas are also a great location for weddings and special events in Tuscany.

Car rentals all over Tuscany and Florence

Florence & Tuscany tours

Florence Lucca Pisa Siena Arezzo Grosseto Livorno Pistoia Montecatini Terme San Gimignano Cortona Montepulciano Volterra Casentino Chianti Garfagnana Lunigiana Maremma Mugello Val d'Orcia Versilia Elba Island Etruscan Coast Crete Senesi Argentario